I've probably seen Woody Allen's 1977 Annie Hall over 100 times. It's a movie I often use as a litmus test with people as to whether or not they'd be able to handle my slightly darker views on people, relationships and life. Like most of Woody Allen's early films, it answers questions about the universe and our roles within it and faces the bleak emptiness of human existence, and it laughs in its face, through shivers and tears. A truly beautiful movie, his first love story, "[he] took a risk; he let the audience feel the sadness of goodbye in a funny movie," as Ms. Keaton says in her book.
The movie charts the relationship of Alvy Singer (Allen), a successful New York comedian, and Annie Hall (Keaton), a ditsy, well-intentioned but aimless aspiring performer originally from Chippewa Falls, Wisconsin, and starts at the end, revealed to the audience through a monologue by Alvy. Annie is as unconventionally dressed as she is behaved, in loose-fitting men's clothing, largely inspired by Keaton's personal wardrobe and sparking a major fashion trend that's still a common reference point today. After a meet-cute playing tennis, the two begin seeing one another, and he encourages her to sing and get out of her apartment and see more people and, of course…because it's Woody Allen, face mortality.